Dimethylformamide → HCID 21705568, compound

HRID 1595957Notes

Reaction equation

HRID 1595957 reaction equation
[OH:1][C@H:2]([CH2:7][OH:8])[CH2:3][C:4]([NH2:6])=[O:5].CN(C)C=O.[C:14](Cl)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Cl-].[Ca+2].[Cl-]>O1CCCC1.N1C=CC=CC=1>[OH:1][CH:2]([CH2:7][O:8][C:14]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH2:3][C:4]([NH2:6])=[O:5]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6456Trityl chlorideHCID 2733882HCID 2733882, compoundHCID 5284359Calcium Chloride

Product 1

HCID 21705568HCID 21705568, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

11.9 g (0.10 mol) (S)-3,4-dihydroxy-butyramide was dissolved in 50 ml of tetrahydrofuran and 50 ml of dimethylformamide and 10 ml of pyridine followed by 30.6 g (0.11 mol) of trityl chloride was added to the flask. A drying tube filled with calcium chloride was used to exclude moisture. The reaction mixture was stirred at room temperature for 36 hours. After this period of time, it was filtered to remove the solid. The liquid was concentrated under reduced pressure to remove most of the solvent. The solution was poured into ice water, stirred for half an hour and the water layer was removed from the trityl protected amide. The product which was obtained as a semicrystalline liquid was dried under vacuum. The excess trityl chloride was washed away by trituration with hexane. The yield was 33.0 g (91%). Physical data: m.p. 59.0-60.0° C. (from solvent dichloromethane:hexane:acetone=6:3:0.5) [α]25D=−53.5° (c=0.5,, methanol). 1H NMR (300 MHz, CDCl3) δppm, 7.50-7.20 (m, 15 H), 6.17 (s, 1H), 5.62 (s, 1H), 4.19 (m, 1H), 3.17 (d, 2H, J=5.7 Hz), 2.41 (m, 2H). 13C NMR (75 MHz, CDCl3) δppm, 174.8, 143.5, 128.3, 127.5, 126.7, 86.3, 67.4, 39.2. FTIR cm−1 3345, 1667, 1600, 1490, 1448, 1218, 1074, 763, 703.

Workup

  1. additionwas added to the flask
  2. filtrationAfter this period of time, it was filtered
  3. customto remove the solid
  4. concentrationThe liquid was concentrated under reduced pressure
  5. customto remove most of the solvent
  6. additionThe solution was poured into ice water
  7. stirringstirred for half an hour
  8. customthe water layer was removed from the trityl
  9. customThe product which was obtained as a semicrystalline liquid
  10. customwas dried under vacuum
  11. washThe excess trityl chloride was washed away by trituration with hexane

Sources & evidence

ORD record
ord-e67569fcc16d4c43bf4159e119da6ec7
Source dataset
uspto-grants-2001_09
Patent number
US06288239B1

Reaction notes

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